1.0 2016-09-30 22:51:07 UTC 2020-05-11 22:30:07 UTC BMDB0002092 BMDB02092 Itaconic acid Itaconic acid, also known as itaconate, belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain. Itaconic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Itaconic acid exists in all living species, ranging from bacteria to humans. 2-Methylenesuccinic acid 2-Propene-1,2-dicarboxylic acid Methylenebutanedioic acid Methylenesuccinic acid Propylenedicarboxylic acid 2-Methylenesuccinate 2-Propene-1,2-dicarboxylate Methylenebutanedioate Methylenesuccinate Propylenedicarboxylate Itaconate 2-Hydroxy-3-naphthoyl-2-naphthylamine Itaconic acid, copper salt Itaconic acid, disodium salt Itaconic acid, calcium salt Itaconic acid, sodium salt C5H6O4 130.0987 130.02660868 2-methylidenebutanedioic acid itaconic acid 97-65-4 OC(=O)CC(=C)C(O)=O InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9) LVHBHZANLOWSRM-UHFFFAOYSA-N belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Branched fatty acids Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Unsaturated fatty acids Aliphatic acyclic compound Branched fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Unsaturated fatty acid Aliphatic acyclic compounds Dicarboxylic acids dicarboxylic acid Solid melting_point 175 °C water_solubility 76.8 mg/mL at 20 °C logp 0.00 ALOGPS logs -0.31 ALOGPS logp 0.053 ChemAxon pka_strongest_acidic 3.65 ChemAxon iupac 2-methylidenebutanedioic acid ChemAxon average_mass 130.0987 ChemAxon mono_mass 130.02660868 ChemAxon smiles OC(=O)CC(=C)C(O)=O ChemAxon formula C5H6O4 ChemAxon inchi InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9) ChemAxon inchikey LVHBHZANLOWSRM-UHFFFAOYSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 27.91 ChemAxon polarizability 11.06 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsIr 1601 Specdb::MsIr 1602 Specdb::MsIr 1603 Specdb::CMs 1051 Specdb::CMs 2916 Specdb::CMs 31391 Specdb::CMs 31984 Specdb::CMs 38263 Specdb::CMs 131007 Specdb::CMs 138741 Specdb::NmrOneD 1850 Specdb::NmrOneD 4686 Specdb::NmrOneD 4714 Specdb::NmrOneD 4953 Specdb::NmrOneD 4954 Specdb::NmrOneD 109338 Specdb::NmrOneD 109339 Specdb::NmrOneD 109340 Specdb::NmrOneD 109341 Specdb::NmrOneD 109342 Specdb::NmrOneD 109343 Specdb::NmrOneD 109344 Specdb::NmrOneD 109345 Specdb::NmrOneD 109346 Specdb::NmrOneD 109347 Specdb::NmrOneD 109348 Specdb::NmrOneD 109349 Specdb::NmrOneD 109350 Specdb::NmrOneD 109351 Specdb::NmrOneD 109352 Specdb::NmrOneD 109353 Specdb::NmrOneD 109354 Specdb::NmrOneD 109355 Specdb::NmrOneD 109356 Specdb::NmrOneD 109357 Specdb::MsMs 1996 Specdb::MsMs 1997 Specdb::MsMs 1998 Specdb::MsMs 5708 Specdb::MsMs 5709 Specdb::MsMs 5710 Specdb::MsMs 5711 Specdb::MsMs 5712 Specdb::MsMs 5713 Specdb::MsMs 21296 Specdb::MsMs 21297 Specdb::MsMs 21298 Specdb::MsMs 22847 Specdb::MsMs 22848 Specdb::MsMs 22849 Specdb::MsMs 437948 Specdb::MsMs 437949 Specdb::MsMs 437950 Specdb::MsMs 437951 Specdb::MsMs 437952 Specdb::MsMs 439208 Specdb::MsMs 2238165 Specdb::MsMs 2240306 Specdb::MsMs 2241417 Specdb::MsMs 2242387 Specdb::NmrTwoD 1095 Specdb::NmrTwoD 1790 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. 25108860 Milk Milk from Friesuan Holstein cows (n=1035) Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Milk By GC-TOFMS and UPLC-QTOFMS Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. 27999311 Ruminal Fluid Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 FDB012645 789 811 30838 C00490 C00033964 35130 Itaconic_acid 6483 ITACONATE Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. 25108860 Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. 27999311